Monoazo dyes having an aryloxyalkyl group on the nitrogen atom in the para position of a 1,4-phenylene coupling component radical

Abstract

Sparingly water-soluble azo compounds of the formula ##STR1## wherein D is phenyl, substituted phenyl, thiazolyl, substituted thiazolyl, benzothiazolyl, substituted benzothiazolyl, 1,3,5-thiadiazolyl, phenyl-1,3,4-thiadiazolyl, nitrobenzoisothiazolyl or substituted thienyl, Wherein each substituent of substituted phenyl, substituted thiazolyl and substituted benzothiazolyl is independently chloro, bromo, nitro, cyano or methylsulfonyl and each substituent of substituted thienyl is independently nitro or acetyl, R 1 is hydrogen, alkyl, alkoxy or --NH--Y--R 5 , wherein Y is --CO--, --COO-- or --SO 2 --, and R 5 is alkyl, haloalkyl, phenyl or substituted phenyl, R 2 is hydrogen or alkoxy, R 3 is phenoxyalkyl, substituted phenoxyalkyl, benzyloxyalkyl or substituted benzyloxyalkyl, and R 4 is hydrogen, cyclohexyl, alkyl or alkyl substituted by chloro, bromo or --O--CO--NH--R 6 , wherein R 6 is alkyl or phenyl are eminently suitable for application as disperse dyes. From aqueous dispersion such dyes build up powerfully on regenerated fibres and synthetic fibres of high molecular weight and hydrophobic character. Dyeings are obtained which are fast to thermofixation, sublimation, pleating, gas fumes, dry cleaning and wet treatments.

Having thus disclosed the invention what we claim is: 
     
       1. A compound of the formula wherein   R 4  is hydrogen, methyl, ethyl or cyclohexyl,   R 11  is hydrogen, chloro or bromo, and   R 12  is hydrogen or chloro.   
     
     
       2. A compound according to claim 1 wherein R 4  is ethyl,   R 11  is hydrogen, chloro or bromo, and   R 12  is hydrogen or chloro, with the proviso that R 11  can be bromo only when R 12  is chloro.   
     
     
       3. A compound of the formula ##STR14## wherein R 11   '  is hydrogen or chloro, and R 12   '  is hydrogen or chloro.   
     
     
       4. The compound according to claim 3 having the formula ##STR15## 
     
     
       5. The compound according to claim 2 having the formula ##STR16## 
     
     
       6. The compound according to claim 2 having the formula ##STR17## 
     
     
       7. The compound according to claim 2 having the formula ##STR18## 
     
     
       8. The compound according to claim 2 having the formula ##STR19## 
     
     
       9. The compound according to claim 3 having the formula ##STR20## 
     
     
       10. The compound according to claim 3 having the formula ##STR21##